- Adaptation Displacement: Loosely based on a picture book by Angus Oblong, Creepy Susie And 13 Other Tragic Tales For Troubled Children, but the show is more well-known at this point.
- Crosses the Line Twice: The show swings between the two all the time. The material is so over the top because otherwise it would be more horrific and depressing than it already is if it were toned down or shown realistically (even though some people who watched the show still thought it was nightmarish and depressing, even if it was shown in such an over-the-top way that it becomes ridiculous.
- Ensemble Dark Horse: Beth and Pickles. The former for being relatively cute, well, by this show's standards anyway. The latter for providing some of the best lines in the show and her status as a former resident of the Hill leaving fans to speculate why she'd give it up. There's surely a story behind it somewhere.
- Harsher in Hindsight: The dichotomy between the rich and poor in the show reached a particularly absurd point in "Flush, Flush, Sweet Helga" when the rich had ready access to clean water that the poor didn't, and proceeded to use it for frivolous purposes like fountains and washing cars. When Helga gets stuck in a different pipe, blocking water for everyone except the Oblong family, the Hills charge an exorbitant amount so only they can afford it. This became slightly less absurd with the water crisis in California. The government has restricted wasteful water-use such as for landscaping, but large houses still have conspicuously-green lawns since the rich just casually pay the large fines on a regular basis.
- Similarly, the Flint, Michigan water crisis in 2015, when it was discovered that State officials were given bottled water months before the issue of contaminated water finally came to light.
- Ho Yay: Jared & Blaine.Milo: Everyone says you two have sex with each other.
- Nausea Fuel:
- In "Narcoleptic Scottie", Helga eats all of Scottie's dog food, delighted that it's the kind that makes its own gravy. We see her with a brown ring of dog food gravy around her mouth.
- In "Disfigured Debbie", Bob is about to change Grammy Oblong's diaper. Bob doesn't have arms, and is accustomed to doing manual tasks with his mouth. Readers are mercifully spared the sight of how he changes the diaper.
- Take That, Scrappy!: Scottie grossing out the Debbies by defecating on the Klimers' lawn in "Narcoleptic Scottie".
- Too Good to Last: It's a testament to this show that it remains one of the bleakest, over-the-top sadistic animated comedies in only 13 episodes, whereas shows like The Simpsons and Family Guy are over-the-top, sadistic, and bleak within a span of 200+ episodes.
- Ugly Cute: Beth.
- Values Dissonance: Bob's displeasure at Milo seemingly becoming a crossdresser in the Li'l Amazons episode, if not him being Transgender, has not aged well at all. Especially when Bob responds to Milo declaring he loves crocheting to him happily asking if Milo could make a noose he can hang himself with.
- Values Resonance: Had the show stayed on for only a couple more years (and didn't get Screwed by the Network), it would have coincided perfectly with a new epidemic of class separation which began mid-Bush administration and continues to this day.
- And in an age where there are more sitcoms and dramas being critically praised for their portrayal of people with disabilities, it is something to remember that there was an animated sitcom about a tight-knit nuclear family with a range of disabilities and disfigurements (limbless, conjoined, odd growths, and OCD).
YMMV / The Oblongs